Literature DB >> 23824256

C-H···O non-classical hydrogen bonding in the stereomechanics of organic transformations: theory and recognition.

Ryne C Johnston1, Paul Ha-Yeon Cheong.   

Abstract

This manuscript describes the role of non-classical hydrogen bonds (NCHBs), specifically C-HO interactions, in modern synthetic organic transformations. Our goal is to point out the seminal examples where C-H···O interactions have been invoked as a key stereocontrolling element and to provide predictive value in recognizing future and/or potential C-H···O interactions in modern transformations.

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Year:  2013        PMID： 23824256     DOI： 10.1039/c3ob40828k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  29 in total

1.  Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors:  Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

2.  Stereocontrol in asymmetric γ-lactam syntheses from imines and cyanosuccinic anhydrides.

Authors:  Ommidala Pattawong; Darlene Q Tan; James C Fettinger; Jared T Shaw; Paul Ha-Yeon Cheong
Journal:  Org Lett       Date:  2013-09-26       Impact factor: 6.005

3.  Torsional steering as friend and foe: development of a synthetic route to the briarane diterpenoid stereotetrad.

Authors:  Nicholas G Moon; Andrew M Harned
Journal:  Org Biomol Chem       Date:  2017-02-22       Impact factor: 3.876

4.  Accessing Multiple Classes of 2 H-Indazoles: Mechanistic Implications for the Cadogan and Davis-Beirut Reactions.

Authors:  Jie S Zhu; Clarabella J Li; Ka Yi Tsui; Niklas Kraemer; Jung-Ho Son; Makhluf J Haddadin; Dean J Tantillo; Mark J Kurth
Journal:  J Am Chem Soc       Date:  2019-04-04       Impact factor: 15.419

5.  Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.

Authors:  Naish Lalloo; Christian A Malapit; S Maryamdokht Taimoory; Conor E Brigham; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2021-10-28       Impact factor: 15.419

6.  Mechanism and Origins of Chemo- and Stereoselectivities of Aryl Iodide-Catalyzed Asymmetric Difluorinations of β-Substituted Styrenes.

Authors:  Biying Zhou; Moriana K Haj; Eric N Jacobsen; K N Houk; Xiao-Song Xue
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

7.  Questions in natural products synthesis research that can (and cannot) be answered using computational chemistry.

Authors:  Dean J Tantillo
Journal:  Chem Soc Rev       Date:  2018-10-29       Impact factor: 54.564

8.  Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Authors:  Ki Po Jang; Gerri E Hutson; Ryne C Johnston; Elizabeth O McCusker; Paul H-Y Cheong; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

9.  Substituent Effects in CH Hydrogen Bond Interactions: Linear Free Energy Relationships and Influence of Anions.

Authors:  Blakely W Tresca; Ryan J Hansen; Calvin V Chau; Benjamin P Hay; Lev N Zakharov; Michael M Haley; Darren W Johnson
Journal:  J Am Chem Soc       Date:  2015-11-19       Impact factor: 15.419

10.  Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.

Authors:  Chang Shu; Honglei Liu; Alexandra M Z Slawin; Cameron Carpenter-Warren; Andrew D Smith
Journal:  Chem Sci       Date:  2019-10-23       Impact factor: 9.825
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